This paper aims to investigate the origin, development, and usage of the postpositional articles in Istro-Romanian, one of the Romanian historical dialects, a likewise dislocated member of the Balkan sprachbund. First, based on the available literature, the evolution of the postpositional articles in the Romance languages will be demonstrated, followed by the evolution of the articles in Romanian and Istro-Romanian, and the languages of the Balkan sprachbund. Afterwards will follow a corpus-based analysis of the similarities and dissimilarities regarding the usage of the postpositional articles in Romanian and Istro-Romanian. It will be based on the parallel texts in Romanian and Istro-Romanian from the Densusianu’s and Pușcariu’s collections. To distinguish as accurately as possible the stages of Istro-Romanian articles, Greenberg’s methodology will be used. That is, his cycle of the grammaticalization of the articles will be applied. It is expected that the analysis will show that despite many centuries of foreign influence, the usage of the postpositional articles in Istro-Romanian is congruent to the usage of the postpositional articles in Romanian and other languages of the Balkan sprachbund.